(a) Interpretation: The major monobromination product that would be obtained when methylcyclohexane is treated with bromine and light is to be predicted. The explanation for the corresponding answer is to be stated. Concept introduction: Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

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Answer 1

Question

Chapter 9, Problem 9.43P

Interpretation Introduction

(a)

Interpretation:

The major monobromination product that would be obtained when methylcyclohexane is treated with bromine and light is to be predicted. The explanation for the corresponding answer is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Interpretation Introduction

(b)

Interpretation:

The relative amounts of the three possible monochlorination product of the photochlorination of triptane is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

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(1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case?

3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) dimethyl sulfoxide (DMSO) is used in place of methanol (b) methanol is used by itself without sodium methoxide (c) 1-chloro-2,2,-dimethylpropane is used in place of 3-chloro-2-methylpropene

3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) the same quantities of reagents are dissolved in half the volume of methanol (b) 3-bromo-2-methylpropene is used in place of 3-chloro-2-methylpropene (c) sodium methanethiolate (CH3SNa) is used in place of of sodium methoxide

Answer 2

Question

Chapter 9, Problem 9.43P

Interpretation Introduction

(a)

Interpretation:

The major monobromination product that would be obtained when methylcyclohexane is treated with bromine and light is to be predicted. The explanation for the corresponding answer is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Interpretation Introduction

(b)

Interpretation:

The relative amounts of the three possible monochlorination product of the photochlorination of triptane is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

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Answer 3

Question

Chapter 9, Problem 9.43P

Interpretation Introduction

(a)

Interpretation:

The major monobromination product that would be obtained when methylcyclohexane is treated with bromine and light is to be predicted. The explanation for the corresponding answer is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Interpretation Introduction

(b)

Interpretation:

The relative amounts of the three possible monochlorination product of the photochlorination of triptane is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

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Answer 4

Question

Chapter 9, Problem 9.43P

Interpretation Introduction

(a)

Interpretation:

The major monobromination product that would be obtained when methylcyclohexane is treated with bromine and light is to be predicted. The explanation for the corresponding answer is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Interpretation Introduction

(b)

Interpretation:

The relative amounts of the three possible monochlorination product of the photochlorination of triptane is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

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Answer 5

Chapter 9, Problem 9.43P

Interpretation Introduction

(a)

Interpretation:

The major monobromination product that would be obtained when methylcyclohexane is treated with bromine and light is to be predicted. The explanation for the corresponding answer is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Interpretation Introduction

(b)

Interpretation:

The relative amounts of the three possible monochlorination product of the photochlorination of triptane is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Answer 6

Chapter 9, Problem 9.43P

Interpretation Introduction

(a)

Interpretation:

The major monobromination product that would be obtained when methylcyclohexane is treated with bromine and light is to be predicted. The explanation for the corresponding answer is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Answer 7

Chapter 9, Problem 9.43P

Interpretation Introduction

(a)

Interpretation:

The major monobromination product that would be obtained when methylcyclohexane is treated with bromine and light is to be predicted. The explanation for the corresponding answer is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The relative amounts of the three possible monochlorination product of the photochlorination of triptane is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The relative amounts of the three possible monochlorination product of the photochlorination of triptane is to be stated.

Concept introduction:

Free radical halogenation of alkane is a reaction in which free radicals are generated to precede the reaction. The halogen molecule first undergoes homolytic bond cleavage to form two halogen radicals, then these halogen radicals initiate the reaction by forming alkyl radical. The reaction then further propagates.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 9 - Prob. 9.1P Ch. 9 - Prob. 9.2P Ch. 9 - Prob. 9.3P Ch. 9 - Prob. 9.4P Ch. 9 - Prob. 9.5P Ch. 9 - Prob. 9.6P Ch. 9 - Prob. 9.7P Ch. 9 - Prob. 9.8P Ch. 9 - Prob. 9.9P Ch. 9 - Prob. 9.10P

Solution Summary: The author explains that the major monobromination product of methylcyclohexane is to be predicted when it is treated with bromine and light.

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